Mannich reactions using benzyl azide as a latent N- (phenylamino)methylating agent

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7687-7690

  Schildknegt, Klaas ^a   Agrios, Konstantinos A ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIDE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; IMINE; MANNICH BASE; PHENYL GROUP; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032532232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01721-3     Document Type: Article

References (13)

1. (1) Recent reviews of the Mannich reaction: (a) Tramontoni, M.; Angiolini, L. Tetrahedron 1990, 46, 1791-1837.
2. (b) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 893-951.
3. (c) Arend, M.; Westerman, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044-1070.
4. (2) Aubé, J.; Milligan, G. L.; Mossman, C. J. J. Org. Chem. 1992, 57, 1635-1637.
5. (3) Previous examples of Mannich reactions that involve the intermediacy of 4 include: (a) Grieco, P.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858.
6. (b) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987-996.
7. (c) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902-6904.
8. (4) Tanino, K.; Takahashi, M.; Murayama, K.; Kuwajima, I. J. Org. Chem. 1992, 57, 7009-7010.
9. (5) Pearson, W. H.; Fang, W.-k. Isr. J. Chem. 1997, 37, 39-46.
10. 3 in DMF at room temperature. CAUTION: All organic azides should be treated as potential explosion hazards.
11. 3b
12. (7) House, H. O.; Trost, B. M. J. Org. Chem. 1964, 29, 1339-1341.
13. (8) Gracias, V.; Frank, K. E.; Milligan, G. L.; Aubé, J. Tetrahedron 1997, 53, 16241-16252.